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Tax Strategies

Letter from the IRS – What You Should Do

Getting a letter from the IRS is almost never a pleasant experience. Even though I run a pretty tight ship when it comes to my tax return, I’ll admit that I get a little nervous when I see that the Treasury department wants to have a word or two with me.  I do my best [...]

How to Pay the IRS with a Credit Card for Free

You know that Uncle Sam is expecting your tax payment shortly. And if you want to make that payment by using your credit card, you can actually do so free of charge and avoid IRS trouble.  If you’re lucky, you might even be able to scoop up some airline miles for yourself too. Have I [...]

What Is Tax Deferral?

What is tax deferral and is it a good thing?  The definition is very straightforward.  Tax deferral is simply a legally acceptable way of putting off paying taxes.  That’s the easy part. What makes tax deferral so darn powerful? You invest to get a return on your money – to make a profit. Sometimes the [...]

When Roth IRA Conversions Make Sense and When They Don’t

The following post has been completely updated from the original version that appeared on January 25, 2010.  Tax-free income at retirement – who wouldn’t want that if they could get it? And you can if your money is invested in a Roth IRA. That’s why Roth IRA conversions are a hot topic. With the Roth, any [...]

Should We Increase Taxes on the Rich

The government is on a desperate search to put as many shekels as it can in its coffer. Is raising taxes on the rich the answer? Most people don’t think so. AP conducted a poll to find out what the best solution was for the deficit problem. 62% think the government should cut spending. Only 20% [...]

IRA Roth Conversion Tax – Do This or Else

If you decide that it makes sense to do a conversion to a Roth IRA, you need to pay your IRA Roth Conversion tax the right way if you want to avoid penalties. That’s right.  Not only do you have to pay “the MAN,” but you also have to do it the way he tells you [...]

How and When to File for a Tax Extension – And Why It’s a Bad Idea

It’s easy to file for a tax extension – but, as you’ll see, you should do everything in your power to file your taxes on time.  Don’t file for an extension if you can help it. First, the easy part. Let’s discuss how it’s done. The benevolent folks at the IRS provide Form 4868, which [...]

How to Get a Full Tax Deduction for Your 529 Contributions

You can actually get a full tax deduction for your 529 contributions.  That’s right, in special circumstances, if you are fortunate and if you’re clever, you can actually arrange for those contributions to be tax deductible. Before I tell you how to do that, I need to mention that anyone can establish a 529 plan. [...]

“Where Is My Tax Refund?” Answered Now

You’re probably just like me.  After I’ve paid my taxes on time I want my tax refund ASAP.  The good news is that the IRS is finally getting on track.  If you want to get a speedy IRS tax refund, here is what you need to do: 1. E-File I read recently that 80% of [...]

9 IRS Audit Flags You Must Avoid Like the Plague

No matter how passive or aggressive you are when it comes to filing your tax return, please avoid IRS audit flags.  You hate paying taxes and you’re certainly not alone. But don’t go too far. Some people take “IRS tax relief” too far! The IRS reported that $30 billion is lost every year due to tax cheats, [...]